5 Fashion Rules That Are Now Okay To Break


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Chaiken coat // Lands’ End cashmere sweater // blazer designed by me in Vietnam // Zara pants (similar here) // Cole Haan heels // ICU sunglasses (c/o) // Mansur Gavriel bag // Meredith Kahn earring

I’m not one to follow the rules—at least when it comes to fashion. I recall wearing head to toe white in winter when I was 10 years old because I dressed myself and wanted to be daring. Little did I know, that was a HUGE fashion faux pas back in the day. These days, all of the “rules” we once were told when it comes to fashion seem to be outdated. Maybe it’s because in this online socially connected age we live in, we are trying to shock and out-do more than ever.

I recently received a confused response from my friend Patrick after I posted an Instagram shot of me wearing white sneakers…in late fall. He was surprised that I, of all people, a wardrobe stylist, would actually wear white after Labor Day. I explained that this rule was completely outdated and in fact most of the fashion rules once engrained in our heads from previous generations have been much more relaxed, or even rebelled against these days.

Here are 5 of those former rules and the new “rules” on how to break them (including the ones I broke here!):



OLD RULE: You can’t mix black and blue or black and brown in your outfit together.

NEW RULE: You totally can and actually it’s quite chic to do so.

This antiquated rule doesn’t make much sense why it’s a rule in the first place. All of these colors act as neutrals in an outfit, so it’s acceptable to wear them together.


OLD RULE: You CANNOT wear white after Labor Day.

NEW RULE: You should really wear more white after Labor Day.

This rule should be left for your grandmother’s generation, thanks to magazines that made the rule popular that white, especially in shoes, should only be worn from Memorial Day to Labor Day. While it makes sense, there’s also something called “winter white, ” that with appropriate seasonal fabrics and styles, you can bend this rule.


OLD RULE: Your bag color should always match your belt color.

NEW RULE: Accessories don’t have to be so matchy matchy.

This is another rule that was made popular in the 1950’s. It’s more interesting when you create a look with say a red handbag and black shoes, or break up a set of jewelry with dainty earrings and a chunky necklace from another style.


OLD RULE: Red lipstick should only be worn at night.

NEW RULE: Red lipstick should be worn any time of day.

This hue will instantly polish any look and wake up your face. Even Taylor Swift is rarely seen without a perfectly rouge pout these days. Just keep the rest of your makeup simple and it will be easy to pass for daytime.


OLD RULE: Don’t wear horizontal stripes because it will make you look wider.

NEW RULE: Wear horizontal stripes because it will make you look stylish.

Stripes can actually work in your favor and distract from other areas you’re insecure about. You can also layer with a blazer/jacket to slim it down. Either way, a million Parisians can’t be wrong with this classic style.

Check out a similar outfit I styled for Lands’ End and shop the whole look here.

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